4-Chlorobenzaldehyde → HCID 25109190, compound

HRID 1514919Notes

Reaction equation

HRID 1514919 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[NH:19][CH2:20][CH2:21][OH:22].[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>CO>[CH3:16][C:11]1[CH:10]=[C:9]([NH:8][C:6]([C:5]2[CH:17]=[CH:18][C:2]3[N:1]=[C:28]([C:27]4[CH:30]=[CH:31][C:24]([Cl:23])=[CH:25][CH:26]=4)[N:19]([CH2:20][CH2:21][OH:22])[C:3]=3[CH:4]=2)=[O:7])[CH:14]=[CH:13][C:12]=1[CH3:15]

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 66966120HCID 66966120, compound

Product 1

HCID 25109190HCID 25109190, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-amino-N-(3,4-dimethyl-phenyl)-3-(2-hydroxy-ethylamino)-benzamide (0.1 mL in 0.2 M DMSO solution), 4-chlorobenzaldehyde (0.1 mL in 0.2 M toluene solution) and FeCl3 (0.05 mL in 0.02 M THF solution) was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-(4-chlorophenyl)-3-(2-hydroxy-ethyl)-3H-benzoimidazole-5-carboxylicacid (3,4-dimethylphenyl)-amide: MS (m/z) 420 (M+1).

Workup

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf586cc548534ed1b5fe609882942881
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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